2-巯基-N,N,N-三甲基-乙铵碘化物(1:1) | 7161-73-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-巯基-N,N,N-三甲基-乙铵碘化物(1:1)
• 中文别名: 硫基胆碱碘化物
• 英文名称: thiocholine iodide
• 英文别名: thiocholine；2-(Trimethylazaniumyl)ethane-1-thiolate--hydrogen iodide (1/1)；2-(trimethylazaniumyl)ethanethiolate;hydroiodide
• CAS: 7161-73-1
• 化学式: C₅H₁₄NS*I
• 分子量: 247.143
• InChiKey: CTGNYPVJSIRPLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.37
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  2-巯基-N,N,N-三甲基-乙铵碘化物(1:1) 、 4-硝基苯基乙酸酯 在 十六烷基三甲基溴化铵 作用下， 以 水 、 乙腈 为溶剂， 生成 对硝基苯酚
  参考文献：
  名称：

  Fornasier, Roberto; Tonellato, Umberto, Gazzetta Chimica Italiana, 1982, vol. 112, # 7/8, p. 261 - 266

  摘要：

  DOI：
• 作为产物：
  描述：

  S-碘化丙酰硫代胆碱 在 acetylcholinesterase from Bactrocera dorsalis (Hendel) 、 水 作用下， 生成 2-巯基-N,N,N-三甲基-乙铵碘化物(1:1)
  参考文献：
  名称：

  Purification and Characterization of Acetylcholinesterase from Oriental Fruit Fly [Bactrocera dorsalis (Hendel)] (Diptera:  Tephritidae)

  摘要：

  An acetylcholinesterase (AChE, EC 3.1.1.7) was purified from the head of the insecticide susceptible oriental fruit fly, Bactrocera dorsalis (Hendel), by affinity chromatography of Triton X-100 extract. The degree of purification was about 8183-fold with recoveries of 52%. The molecular mass of purified AChE was 116 kDa for its native protein (nonreduced form) and 61 kDa for its subunits (reduced form) as revealed on sodium dodecyl sulfate polyacrylamide gel electrophoresis (SIDS-PAGE), suggesting that the homodimer of AChE linked with disulfide bonds. Nondenaturing PAGE of the purified AChE revealed only one molecular form. The maximum velocities (V-max) for hydrolyzing acetylthiocholine (ATC), propionylthiocholine, and S-butyrylthiocholine were 833.3, 222.2, and 57.5 mumol/min/mg, and the Michaelis constants (K-m) were 87.9, 26.9, and 195.3 muM, respectively. More than 97% of AChE activity was inhibited by 10 muM eserine or BW284C51, but only 53% of the activity was inhibited by ethopropazine at the same concentration. On the basis of the substrate and inhibitor specificities, the purified enzyme appeared to be a true AChE. Nevertheless, the purified AChE exhibited some distinctive characteristics including (i) a lack of the substrate inhibition phenomenon when using ATC as the hydrolyzing substrate and (ii) a higher V-m value for ATC than AChE from other insect species. These biochemical properties may show that AChE purified from the oriental fruit fly may have structural differences from those of other insect species.

  DOI：

  10.1021/jf0494377

文献信息

• Benzoylthiocholine derivatives as substrates for pseudocholinesterase : Synthesis and application.
  作者：MAGOHEI YAMADA、YOJI MARUI、CHOZO HAYASHI、SHOJI TAKEMURA

  DOI：10.1248/cpb.35.1491

  日期：——

  Substituted benzoylthiocholines were synthesized and their application as reagents for clinical measurement of pseudocholinesterase was investigated. Among 21 compounds, 2, 3-dimethoxybenzoylthiocholine (19b) was found to be an excellent substrate for the measurement of the enzyme. The procedure was simple and self-hydrolysis of the substrate at the optimum pH of the enzyme was minimal.

  合成的取代苯甲酰硫代胆碱化合物，并研究了它们作为临床测量假胆碱酯酶试剂的应用。在21种化合物中，2,3-二甲氧基苯甲酰硫代胆碱（19b）被发现是测量该酶的优秀底物。该方法简便，且底物在酶的最适pH下自水解程度最小。
• Transition State Structure and Rate Determination for the Acylation Stage of Acetylcholinesterase Catalyzed Hydrolysis of (Acetylthio)choline
  作者：Siobhan Malany、Monali Sawai、R. Steven Sikorski、Javier Seravalli、Daniel M. Quinn、Zoran Radić、Palmer Taylor、Chanoch Kronman、Baruch Velan、Avigdor Shafferman

  DOI：10.1021/ja9933590

  日期：2000.4.1

  isotope effects and most inverse substrate isotope effects, proton inventories are linear or nearly so, consistent with prominent rate limitation by a chemical step whose transition state is stabilized by a single proton bridge. Reactions that have smaller solvent isotope effects and less inverse substrate isotope effects have nonlinear and upward bulging proton inventories, consistent with partial rate

  乙酰胆碱酯酶催化水解（乙酰硫基）胆碱的酰化阶段的限速步骤和过渡态结构的特征在于测量底物和溶剂同位素效应以及粘度对双分子速率常数 kE ()kcat/Km 的影响。已经测量了来自加利福尼亚鱼雷、人和小鼠的野生型酶以及这些酶的各种活性位点突变体的底物和溶剂同位素效应。当底物β-氘同位素效应最相反时，观察到相当大的溶剂同位素效应，D2O kE 2，δ kE ) 0.95；相反，具有 D2O kE 1 的反应具有 ‚D kE ) 1.00 的底物同位素效应。kE 的质子清单提供了连续步骤贡献的定量测量，底物与活性位点的扩散接触和随后的化学催化，以限制催化酰化阶段的速率。对于具有最大溶剂同位素效应和大多数逆底物同位素效应的反应，质子存量是线性的或接近线性的，这与过渡态由单个质子桥稳定的化学步骤的显着速率限制一致。具有较小溶剂同位素效应和较少逆底物同位素效应的反应具有非线性和向上膨胀的质子库存，这与扩
• Delineation and Decomposition of Energies Involved in Quaternary Ammonium Binding in the Active Site of Acetylcholinesterase
  作者：Daniel M. Quinn、Shawn R. Feaster、Haridasan K. Nair、Nathan A. Baker、Zoran Radić、Palmer Taylor

  DOI：10.1021/ja9933588

  日期：2000.4.1

  quaternary ammonium binding locus in the active site of mammalian acetylcholinesterase is subtended by the side chains of Trp86, Tyr133, Glu202, and Tyr337. Linear free-energy relationships define the interactions involved in molecular recognition by mouse acetylcholinesterase of the quaternary ammonium moiety of ligands. For substrates CH3C(O)XCH2CH2Y [X = O, Y = CHMe2, or CH2CH3; X = S, Y = H, NH+Me2

  哺乳动物乙酰胆碱酯酶活性位点中的季铵结合位点由 Trp86、Tyr133、Glu202 和 Tyr337 的侧链包覆。线性自由能关系定义了小鼠乙酰胆碱酯酶对配体季铵部分的分子识别所涉及的相互作用。对于底物 CH3C(O)XCH2CH2Y [X = O, Y = CHMe2, 或 CH2CH3; X = S、Y = H、NH+Me2 或 N+Me3 ] 和三氟苯乙酮过渡态类似物抑制剂 m-YC6H4C(O)CF3 [Y = H、Me、Et、iPr、tBu、 、NH2、NO2、NMe2 ，或 N+Me3]、log(kcat/Km) 和 pKi 与取代基 Y 的摩尔折射率呈线性关系，但与疏水性无关。这些相关性表明，在催化的酰化阶段，季铵结合位点中的相互作用使四面体中间体（由过渡态类似物亲和力建模）稳定（5 × 105）倍（ΔΔGTI = -32.5 kJ mol-1）和过渡态稳定（2 × 104）倍（ΔΔG‡
• Functional micellar catalysis. Part 3. —Quantitative analysis of the catalytic effects due to functional micelles and comicelles
  作者：Roberto Fornasier、Umberto Tonellato

  DOI：10.1039/f19807601301

  日期：——

  The kinetic treatment of reactions catalysed by functional micelles and comicelles made up of chemically inert and functional surfactants, based on the pseudophase separation approach, allows the evaluation of the parameters defining the catalytic phenomena. The rate enhancements of activated ester hydrolysis due to cationic micelles of previously described functional surfactants, when compared to

  基于伪相分离方法，对由化学惰性和功能性表面活性剂组成的功能性胶束和胶束催化的反应进行动力学处理，可以评估定义催化现象的参数。当与由于类似的非胶束模型化合物引起的阳离子胶束相比时，前述功能性表面活性剂的阳离子胶束引起的活化酯水解的速率增强主要可以由浓度和静电效应来解释。去溶剂化和其他对阴离子胶束功能的影响不是速率提高的相关来源。还介绍了在标准条件下分析各种功能性表面活性剂催化效率的可笑溶液的优点。
• Synthesis of Reversible Inhibitors of Acetylcholinesterase (EC 3.1.1.7)
  作者：Peter Thanei-Wyss、Peter G. Waser

  DOI：10.1002/hlca.19830660731

  日期：1983.11.2

  The synthesis and characterization of some reversible acetylcholinesterase inhibitors are described in detail. They are structurally related to the natural substrate acetylcholine. All of them bear a trimethylammonium moiety as ‘cationic head’. Instead of an electrophilic ester group, the title compounds include a variety of functionalities, such as halide, ether, thioether, epoxide, amide, ketone

  详细描述了一些可逆的乙酰胆碱酯酶抑制剂的合成和表征。它们在结构上与天然底物乙酰胆碱有关。它们全部带有三甲基铵部分作为“阳离子头”。代替亲电子酯基，标题化合物包括各种官能团，例如卤化物，醚，硫醚，环氧化物，酰胺，酮和双键。因此，这些物质适合用作研究乙酰胆碱酯酶活性中心的酯基亚位点的探针。